Ethyl 3-oxo-3-phenyl-2-(trimethylstannylmethyl)propanoate | 154849-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 3-oxo-3-phenyl-2-(trimethylstannylmethyl)propanoate
• CAS: 154849-72-6
• 化学式: C₁₅H₂₂O₃Sn
• 分子量: 369.048
• InChiKey: UTPLPVGMSZSMQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-oxo-3-phenyl-2-(trimethylstannylmethyl)propanoate 在 niobium pentachloride 作用下， 以51%的产率得到4-氧代-4-苯基丁酸乙酯
  参考文献：
  名称：

  Niobium pentachloride-mediated novel homologation reactions using α-trialkylstannylmethyl-β-keto esters

  摘要：

  In the presence of niobium pentachloride (NbCl5), an alpha-trialkylstannylmethyl-beta-keto ester is homologated to the corresponding gamma-keto ester in good yield; the reaction mechanism is discussed.

  DOI：

  10.1039/cc9960002353
• 作为产物：
  描述：

  sodium 3-ethoxy-3-oxo-1-phenylprop-1-en-1-olate 、 trimethylstannylmethyl iodide 以 甲苯 为溶剂， 以60-75的产率得到Ethyl 3-oxo-3-phenyl-2-(trimethylstannylmethyl)propanoate
  参考文献：
  名称：

  2,2-Functionally disubstituted organotin compounds: synthesis and reactivity

  摘要：

  A series of 2,2-difunctional organotin compounds of the general type Me(3)SnCH(2)CHXY (X, Y = P(O)R(2) or C(O)R; R = (OPr)-Pr-i, OEt or Ph) has been synthesized by stannylmethylation of the appropriate 2,2-difunctional methanides Na[CHXY] with iodomethyl trimethylstannane. Derivatives with phenyl groups on tin cannot be made by this method. The reactions of the title compounds at the tin atom and at the acidic CH group of the bridging carbon atom and modifications of the functional P(O)R(2) and C(O)R groups are described.

  DOI：

  10.1016/0022-328x(94)88031-x

文献信息

• Niobium pentachloride-mediated novel homologation reactions using α-trialkylstannylmethyl-β-keto esters
  作者：Makoto Yamamoto、Misako Nakazawa、Keiki Kishikawa、Shigeo Kohmoto

  DOI：10.1039/cc9960002353

  日期：——

  In the presence of niobium pentachloride (NbCl5), an alpha-trialkylstannylmethyl-beta-keto ester is homologated to the corresponding gamma-keto ester in good yield; the reaction mechanism is discussed.
• 2,2-Functionally disubstituted organotin compounds: synthesis and reactivity
  作者：F. Richter、H. Weichmann

  DOI：10.1016/0022-328x(94)88031-x

  日期：1994.2

  A series of 2,2-difunctional organotin compounds of the general type Me(3)SnCH(2)CHXY (X, Y = P(O)R(2) or C(O)R; R = (OPr)-Pr-i, OEt or Ph) has been synthesized by stannylmethylation of the appropriate 2,2-difunctional methanides Na[CHXY] with iodomethyl trimethylstannane. Derivatives with phenyl groups on tin cannot be made by this method. The reactions of the title compounds at the tin atom and at the acidic CH group of the bridging carbon atom and modifications of the functional P(O)R(2) and C(O)R groups are described.